Composition of matter and process of producing the same.



i TED STATES PATENT OFFICE.

LAWRENCE VINCENT REDMAN, OF LAWRENCE, KANSAS, ASSIG-NOR, BY MESNE AS-SIGNMENTS, TO AMBEROID CHEMICAL PRODUCTS COMPANY, OF CHICAGO, ILLI-NOIS, A. CORPORATION WEST VIRGINIA.

COMPOSITION OF MATTER AND IROCESS OF PRODUCING THE SAME.

No Drawing.

7 '0 all whom it may concern:

Be it known that I, LAWRENCE VINCENT REDMAN, a citizen of Canada,residing at Lawrence, in the county of Douglas and State of Kansas, haveinvented a new and useful Improvement in Compositions of Matter andProcesses of Producing the Same, of which the following is aspecification.

The present invention constitutes an improvement 'on the invention setforth in my pending application No. 567 ,353, filed June 17, 1910; andthe primary object of the present invention is to provide an improvedprocess of obtaining a product of the general character set forth in theapplication referred to, with improvedresults in the product.

A product of the character to which the present invention relates isadapted for coating or varnishing surfaces of wood, metal and othermaterials; and the composition of matter is also adapted to serve as abinder, or adhesive, and, in fact, in many situations where a hard,comparatively strong, stable substance, of great chemical and physicalinertness is required. Such product, in its final stage, may be maderesistant to the action of water and known solvents and made infusible.The new composition of matter may be employed as an artificial amber formany purposes, and may be used for making buttons, and also for makingmolding blocks, or dies, for many purposes. Also, the new compositionmay be employed-for insulating purposes, and for other uses too numeroustomention.

In practisingmy invention, I prefer to proceed as follows, that is tosay: Compound or mix together a phenol, such as carbolic acid (C l-LOH),or a homologue, hexamethylenetetramin [(CHQ NJ, an initialproductsolvent, such as denatured alcohol, acetone, or amylacetate, and a smallamount of glycerin, or the like, which is adapted to modify the finalproduct, by lessening the brittleness, or in other words, bycontributing a certain amount of pliability and increasing theelasticity. As an illustration, I may take 90 grams of carbolic acid,dissolve the same in three grams of glycerin (C ,H O mix the same with23 grams of hexamethylenetetramin, and add 80'grams- Specification ofLetters latent.

Application filed February 17, 1911. Serial No. 609,168.

Patented Aug. 18, 1914.

of alcohol; after thus compounding or mixing the ingredients, subjectthe resultant mixture to the action of heat at a temperature of about 80C. for, say, five hours. This initial product may be applied in whateverway desired to surfaces, as a coatmg, or may be used as a binder, glueor adhesive, allowing the alcohol time to evaporate. The initial productmay be subjected to the action of heat at approximately 130 C. to 190 C.under a pressure of from eighty to one hundred and twenty pounds persquare inch or as much greater as desired, maintaining this temperatureand pressure for a period of from thirty minutes to several hours,depending upon the amount of material being treated, to obtain what Iterm the final product. The heat hastens the reaction, and the pressuretends to regulate the ebullition due to the escape of ammonia andmaintain the density of the top portion-of the product. Moreover, theconcentration of the air (compressed air being used for pressurepurposes) has an influence in producing the coloring of the materialbeing treated, due probably to oxidation.

The introduction of the alcohol before the first heat treatment, whichresults in what I may term the initial product, has the importantadvantage that the alcohol will act to retard the reactions and thusrender the process more readily controllable, the alcohol, in the end,serving also to hold the initial product in solution.

.l/Vhen the mixture is subjected to heat at a temperature of about 80(1., it soon changes its condition to a yellowish transparent mobileliquid with a smell of ammonia, and after approximately five hoursheating at such a temperature, results in What I have termed the initialproduct. This product, when produced in the presence of alcohol, is heldin solution by the alcohol'and may be employed as a varnish. After beingapplied in a thin coating and allowed to stand for some time, it changesits characteristics, and becomes somewhat insoluble in known solvents.This initial product, were it not for the presence of the alcohol, wouldbecome viscous after the approximately one-half hours heat treatment ata temperature of 80 C. or thereabout, and would solidify on cooling,being soluble, however, in alcohol. The expression initial product ismeant to' cover the product after the first heat treatment, with orwithout the removal or evaporation of the solvent.

As stated above, the alcohol not only serves, in the end, as a solventfor the initial product, but acts as a controlling agent during thereactions which occur while the heat treatment is in progress. Anysuitable alcohol, or any other suitable solvent which will serve as acontrolling agent during the re-actions which occur while the heattreatment is in progress, may be used.

The glycerin is employed to render the product more pliable and modifythe color, which it does by changing the color to a ruby red. Ifdesired, it may be omitted, however, or some substitute may be employedin lieu of glycerin. Where the glycerin is employed, the carbolic acidmay be dissolved in it; otherwise, it is necessary or desirable to meltthe carbolic acid before mixing it with the l1examethylenetetramin,Certain advantages in the treatment, as Well as in the quality of-theproduct, are attributable to the use of glycerin, or a substitute.

hen it is deslred to produce the final product, by the final heattreatment, thismay be done by virtually continuing the heat treatment,but at a higher temperature, and preferably, although not necessarily,under pressure. After the mixture has been subjected to the hightemperature mentioned, under pressure, for a period of time, theduration of which depends upon the quantity of material being treated,it assumes the condition of a solid which is insoluble in knownsolvents; and, in this state, the substance is adapted for use as asubstitute for amber, and may be employed as an electric insulator, heatinsulator, and for other purposes too numerous to mention.

When the initial product is used for coating purposes, the articlecoated may be baked, if desired, which will hasten the change of thecoating to the insoluble'state, without detriment to the coating. Thebaking may be performed in vacuum, underatmospheric pressure, or underadditional pressure, as desired. During the whole course of treatmentammonia is eliminated from the mixture, and after the ammonia has ceasedto come off, the product soon becomes both insoluble and infusible.Inasmuch as no water is employed in the mixture, and water is not formedat any stage in the process of treatment, formaldehyde is not produced,so that the objections incident to a process where formaldehyde isformed are obviated.

Moreover, the product does not, under treatment, or at any time, tend tostratify or separate into layers of varying characteristics orcomposition. In other Words, a uniform, homogeneous product is secured,and

so far as l[ have been able to determine, only,

ammonia is evolved or given off during the process.

When the product is to be used as a binder for abrasive material, suchas carborundum or asbestos sheets, the heat treatment at .ap proximately80 C. may be continued with the distillation of alcohol until thedesired condition of viscosity is reached. Then aluminum oxid,carborundum, sand, etc., may be added and the mixture baked. Taken atthe same stage, the initial product may be mixed with lead oxid, sand,talc, fullers earth, graphite, or other neutral material, for coating orpainting purposes. Also, in the dissolved conditio'n the initial productmay be mixed with mineral or coal tar dyes, as desired.

The initial product in the dissolved state above set forth may/ beemployed as a substitute for varnishes, lacquers, etc., being applicableto Wooden, metal, cement, and other surfaces. The initial product willserve also as a substitute for glue or cement for uniting surfaces, withimproved results. After the final heat and pressure treatment above setforth, the material is a solid infusible mass, and, in this state, maybe employed as a sort of artificial amber, and, in fact, the compoundmay be put to uses too numerous to mention, wherev a hard infusibleproduct of great chemical inertness is desired, or where material may becalled upon to resist high temperature or the action of acids, 211-kalis or solvents.

When employed as a coating for surfaces, the material gives a very hardlustrous finish, practically transparent and may be practicallycolorless, or may have a varying yellowish amber to deep red tint. Itmay be given a deep red color, if desired, by raising the finaltemperature to 170 C. to 195 C. The finish produced is of glass-likehardness and little liable to danger of scratching, and when thematerial is modified by the use of glycerin, or the like, the materialpossesses suflicient pliability and tenacity to prevent it from crackingor peeling. It may be added that after heating at a high temperature,(second heat treatment) as suggested above, under ressure, the materialpasses, without bubbling, to a transparent, slightly yellowish, amber orred glassy, insoluble and infusible product. The proportions and methodof treatment suggested above are those which have found the most advantaeous, but I desire to be understood as not imiting myself unnecessarily.Again, while I prefer to employ carbolie acid, I ma em loy a homolo ue,such as cresol CH S H OH), or ot er phenolic body. I desire to claim myinvention in sufficiently generic terms to include substitutes. g

It is characteristic of and an advantaiso geous feature of myinventionthat no water is formed durin theprocess, so that the problem ofeliminating such a deleterious element from the mass undergoingtreatment is wholly obviated, and the process is simplified andshortened, the control of the process .is rendered comparatively easy,and the danger of lack of uniformityof texture, composition and thedesirable qualities generally of the final insoluble product islessened. As a matter of fact, the mass possesses homogeneity throughoutduring all stages of the heat treatment, having no tendency to separateor stratify in layers having varying com ositions and qualities.

My process also ren ers unnecessary the introduction of a condensing orcatalytic agent, so that there remains no necessity for eliminating suchagent at the end of the reaction. Moreover, the reaction is anhydrous inmy process, no water being intro duced (as where a solution offormaldehyde amount is too small to seriously afiect the ess are onereacting weight 0 eflicacy of the processor impair the product, so thatpractically it ma c said that the process is anhydrous, as a oveindicated. It

- will be noted that the proportions which are preferably employed inpractisin my proc- I hexamethylenetetramin to more: than five re-ctingweights of the-phenolic body employed, the

henolic body employed being an uncomhined or simple, commerciallyobtainable, ingredient. I do not intend, by the expression phenolic body.to include a condensation product of formaldehyde and phenol,

the production of which would necessitate.

subjecting t the practice of a process having many dis-' advantages.

What I regard as new and desire to secure by- Letters Patent is- 1. Theprocess of producing a phenolic condensation product, which consists incompounding a henolic body, hexamethylenetetramin an an initial-productsolvent which acts also as a controlling agent, and subjecting the same,after compounding, to the action of heat and driving off ammonia.

2. The process of producing a phenolic condensation product, whichconsists in compounding a phenolic body, hexamethylenetetramin and aninitial-product solvent which acts also as a controlling agent, saidhexamethylenetetramin and said phenolic body being used in theproportions of one reacting weight of hexamethylenetetramin to more thanfive molecular weights of said phenolic body, subjecting the same, aftercompounding, tothe action of heat at comaratively moderate temperaturefor a preetermined period of time, and afterward e initial product to ahigher temperature under pressure for a predetermined period of time. 3.The process of producing a phenolic condensation product which consistsin dissolving carbolic acid in a comparatively small quantit ofglycerin, mixing therewith hexamet ylenctetramin, the materials beingemployed in the proportions of more than five 1nolecular weights of'carbolic acid to one of hcxamethylenetetramin, addin to the mixture aninitial-product solvent which acts also as a controlling agent, andsubjecting the mixture to the. action of heat for a period of time.

4. The process of producing a phenolic condensation product whichconsists in com pounding a phenolic bod hexamethylenetetramin and aninitia )roduct solvent which acts also as a control ing agent, thesesubstances being compounded substantially in the absence of water, andsubjecting the mixture in such condition to the action of heat andthereby driving 08: ammonia.

LAWRENCE VINCENT REDMAN.

In presence of-- HUGH BLAIR, JENN r. WA'I'I.

